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由香茅醛到保幼激素类似物ZR-515的简便全合成

A FACILE ROUTE FOR TOTAL SYNTHESIS OF THE JUVENILE HORMONE ANALOGUE ZR-515 FROM CITRONELLAL

  • 摘要: 以香茅醛为起始原料,首先与丙酮进行羟醛缩合反应,继而在金属锌的存在下与α-溴乙酸乙酯进行Reformatskii反应得到目标碳链,然后再经水解、酯化和醚化,最终成功地全合成了具有保幼激素活性的昆虫生长调节剂ZR-515及其异构体,即11-甲氧基-3,7,11-三甲基-(2E,4E)-十二碳二烯酸异丙酯。其中具有较高生物活性的(2E,4E)-异构体(ZR-515)的含量达56%。各步所合成化合物的结构经IR、MS、1HNMR证实。

     

    Abstract: Dimethylundeca-3,9-dien-2-one was prepared from the starting material citronellal reacting with acetone via aldol condensation, followed by reacting with α-bromoethyl acetate in the presence of Zn through Reformatskii reaction to obtain target chain. After hydrolysis, esterification and etherification, the isomeric products, isopropy-11-methoxy-3,7,11-trimethy1-(2E,4E)-dodecadienoate, which possess juvenile hormone activity, were succeededly synthesized, in which the (2E,4E)-stereoisomer ZR-515, which showed considerably higher activity than other isomers, amounted to 56%. The structures of all compounds in each step were confirmed by 1H NMR、IR and MS.

     

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